The biggest assholes on film

Ditch that moral compass with ten of the biggest cinematic slimeballs ever to have graced the big screen

A fool's born every minute, right? The same could be said of assholes, and there are so many in film that this could never come close to an exhaustive list. But if the glut of aspirational role models you're meant to strive to measure up to is making you gag, this catalogue of screen slimeballs past and present – smug, smarmy and with no moral compass – could offer a breather. You're practically an angel after all.

DEVEREAUX IN WELCOME TO NEW YORK (2014)

"Don't you know who I am?" grunts a semi-naked Gerard Depardieu. Power might be intoxicating in some situations, but in this canny take on the Dominique Strauss-Kahn case, it's just gross. Director Abel Ferrara, who had portrayed the ultimate corrupt cop in iconic '90s indie Bad Lieutenant, here revisits lurid bad behaviour to paint a personality so used to utter unaccountability and anything-goes rentable orgies that when a hotel housemaid resists his lumbering come-on, his facade of respectability combusts. Out in the UK on Friday.

COURTNEY SHAYNE IN JAWBREAKER (1999)

"She was like Satan in heels." Courtney (Rose McGowan) is the ice-blooded ringleader of the popular clique at Reagan High School. When they accidentally kill their friend Liz during a mean prank involving jawbreaker hard candy, they try to cover up the crime, in this pitch-black comedy from Darren Stein. Check out our interview with Rose and Darren on Jawbreaker's killer legacy.

STEFF MCKEE IN PRETTY IN PINK (1986)

Being an asshole, high school rich kid Steff McKee (James Spader, his hotness wasted on a dud personality) thinks the only legit way to react when his come-on his rejected by Andie (Molly Ringwald) is to seek underhand revenge. Doubly humiliated that she's from a less financially flush social clique, he ridicules her thrift-store style when she hooks up with his decent-acting best friend (Andrew McCarthy) in this John Hughes classic.

JORDAN BELFORT IN THE WOLF OF WALL STREET (2013)

"Greed is good" was a line immortalised by ruthless corporate raider Gordon Gecko (Michael Douglas) in Oliver Stone's Wall Street, summing up the mood of the indulgent '80s. Smarmy stockbroker Jordan Belfort is in Scorsese's exuberant but never glamourising take on a real-life memoir an equivalent for our times. In an irreverent onslaught of lurid, tacky behaviour the grotesque side of depraved corruption holds sway.

James Simon looks a dead ringer for clerk Simon James, but being a charming extrovert is able to slime his way into all aspects of his life, taking them over to the point Simon starts to lose his mind. A gloomy, labyrinthine office that's all shades of Kafka is the prime setting for this pitch-black comedy of persecution at the hands of covetous assholery, directed by Richard Ayoade and based on a 19th-century Russian novella by Fyodor Dostoevsky.

Before Courtney Shayne, there was Heather Chandler (Kim Walker), leader of the notorious high-school clique of popular girls called Heather in Michael Lehmann's wickedly savage black comedy and purveyor of such casual soundbites as "Bulimia's so '87" and "Fuck me gently with a chainsaw". She's formidable – until the arrival of new member Veronica (Winona Ryder), who very soon tires of her bullshit.

ALEX DELARGE IN A CLOCKWORK ORANGE (1971)

Casual cruelty as revelry is the M.O. of amoral young thug Alex (Malcolm McDowell), who goes on an ultra-violent crime spree with his gang of delinquent droogs, fuelled by drug-laced milk. Is there a cure for such urges? Stanley Kubrick's vicious dystopian satire on social control questions the lengths the state may go to in creating a state of passively acquiescent citizens.

MILDRED RATCHED IN ONE FLEW OVER THE CUCKOO'S NEST (1975)

If there's one supreme asshole on film, it has to be the deceptively bland but icy nurse that lords over the mental institution ward anti-establishment crim Mac (Jack Nicholson) inspires to rebellion in this Ken Kesey classic. This demonised, powerful female, played by Louise Fletcher, is probably a reactionary creation of an era in which women were gaining greater freedoms - but whatever the roots, she couldn't sum up repellently inhuman bureaucracy more chillingly.

KATHARINE PARKER IN WORKING GIRL (1988)

Asshole bosses can turn any office into a snakepit. Fashion mag editor Miranda Priestley's pathologically demanding reign of terror in The Devil Wears Prada is bad enough, but the idea-stealing financial exec in this Mike Nichols classic takes the cake for brazen career obstruction. Knowing conventional office rules will get her nowhere, working-class secretary Tess (Melanie Griffith) outsmarts her corrupt boss Katharine (Sigourney Weaver), without taking on her cutthroat methods when she finally makes it.

THE MARBLES IN PINK FLAMINGOS (1972)

No label seems adequate to describe Connie and Raymond Marble (Mink Stole and David Lochary), though they themselves are hellbent on winning the title of "Filthiest People Alive" - a questionable honour a sleazy tabloid paper has conferred on flashy crim Babs Johnson (Divine). Bad taste king John Waters goes all out in this darkly comic, gaudy no-budget classic as the Marbles – who love each other "more than the sound of death rattle" – lay down the gauntlet, and all hell breaks loose. We got Mink to take our USA-themed pop quiz last month, catch her talking high school hell and working with John Waters here.